The oxylipin chemistry of the temperate red alga Polyneura latissima has been investigated. The structures of three novel oxylipins, 8-[1'(Z),3'(Z),6'(Z)-dodecatriene-1'-oxy]- 5(Z),7(E)-octadienoic acid, 7(S*)-hydroxy-8(S*),9(S*)-epoxy-5(Z),11(Z),14(Z)-eicosatrienoic acid, 7(R*)-hydroxy-8(S*),9(S*)-epoxy-5(Z),11(Z),14(Z)-eicosatrienoic acid, together with two known eicosanoids, 9(S)-hydroxy-5(Z),7(E),11(Z),14(Z)-eicosatetraenoic acid, and 9,15-dihydroxy-5(Z),7(E),11(Z),13(E)-eicosatetraenoic acid, were elucidated by spectroscopic methods and chemical degradation. The oxygenation pattern of these oxylipins suggests that P. latissima metabolizes polyunsaturated fatty acids via a 9(S)-lipoxygenase.